Furoxan - Misplaced Pages

Furoxan
Names

Preferred IUPAC name 1,2λ,5-Oxadiazol-2-one
Other names Furazan N-oxide; Furazan 2-oxide
Identifiers
CAS Number	497-27-8
3D model (JSmol)	Interactive image
ChemSpider	4482868
MeSH	C528141
PubChem CID	5325374
CompTox Dashboard (EPA)	DTXSID80416009
InChI InChI=1S/C2H2N2O2/c5-4-2-1-3-6-4/h1-2HKey: KCMCIQNPQUSQKQ-UHFFFAOYSA-N InChI=1/C2H2N2O2/c5-4-2-1-3-6-4/h1-2HKey: KCMCIQNPQUSQKQ-UHFFFAOYAH
SMILES 1=CC=NO1
Properties
Chemical formula	C₂H₂N₂O₂
Molar mass	86.050 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Furoxan or 1,2,5-oxadiazole 2-oxide is a heterocycle of the isoxazole family and an amine oxide derivative of furazan. It is a nitric oxide donor. As such, furoxan and its derivatives are actively researched as potential new drugs (Ipramidil) and insensitive high density explosives (4,4’-Dinitro-3,3’-diazenofuroxan).

Furoxanes can be formed by dimerization of nitrile oxides.

References

Clara Cena; Massimo Bertinaria; Donatella Boschi; Marta Giorgis; Alberto Gasco (2006). "Use of the furoxan (1,2,5-oxadiazole 2-oxide) system in the design of new NO-donor antioxidant hybrids" (PDF). Arkivoc (HL-1787GR): 301–309.

sGC	Activators/stimulators: Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat Inhibitors: ODQ

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N-(1-Iminoethyl)-L-ornithine (L-NIO) N-Methyl-L-arginine (L-NMA) N-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N-(1-Iminoethyl)-L-ornithine (L-NIO) N-(1-Iminoethyl)-L-lysine (L-NIL) N-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM
eNOS	Aminoguanidine (pimagedine) N-(1-Iminoethyl)-L-ornithine (L-NIO) N-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)
Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381

Others

Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
ET_B receptor antagonists (e.g., bosentan)
L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g., sildenafil)
non-selective PDE inhibitors (e.g., caffeine)
PDE9 inhibitors (e.g., paraxanthine)
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
Statins (e.g., simvastatin)

See also: Receptor/signaling modulators

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